Crystal structure of 2-methyl-1,2,3,4-tetra­hydro­iso­quinoline trihydrate

The crystal structure of the title heterocyclic amine was determined in the presence of water. The compound co-crystallizes with three water mol­ecules in the asymmetric unit, which leads to the formation of hydrogen bonding in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.109
• Data-to-parameter ratio = 20.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2020), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2008).

2-Methyl-1,2,3,4-tetrahydroisoquinoline trihydrate

Crystal data

C10H13N·3H2O	F(000) = 440
Mr = 201.26	Dx = 1.162 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.1791 (19) Å	Cell parameters from 5564 reflections
b = 5.9209 (6) Å	θ = 2.6–30.5°
c = 12.5007 (14) Å	µ = 0.09 mm^−1
β = 106.093 (5)°	T = 100 K
V = 1150.6 (2) Å^3	Needle, colourless
Z = 4	0.51 × 0.09 × 0.05 mm

Data collection

Bruker D8 Venture diffractometer	3350 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	2708 reflections with I > 2σ(I)
HELIOS mirror optics monochromator	Rint = 0.042
Detector resolution: 10.4167 pixels mm^-1	θmax = 30.0°, θmin = 2.6°
ω and φ scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −8→8
Tmin = 0.655, Tmax = 0.746	l = −17→17
13488 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: mixed
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.3326P] where P = (Fo^2 + 2Fc^2)/3
3350 reflections	(Δ/σ)max = 0.001
160 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.59406 (5)	1.05257 (14)	0.81663 (7)	0.02252 (18)
H1D	0.6378 (12)	0.971 (3)	0.7983 (16)	0.056 (5)*
H1E	0.5579 (14)	1.109 (4)	0.7482 (19)	0.074 (6)*
O3	0.39039 (6)	0.63708 (15)	1.01569 (7)	0.02562 (19)
H3C	0.4235 (13)	0.685 (3)	0.9772 (17)	0.062 (6)*
H3D	0.3929 (13)	0.744 (4)	1.0688 (17)	0.062 (6)*
O2	0.50431 (6)	0.71399 (15)	0.88618 (7)	0.02490 (19)
H2C	0.5355 (14)	0.830 (4)	0.8673 (17)	0.066 (6)*
H2D	0.5419 (14)	0.609 (4)	0.9175 (17)	0.063 (6)*
N1	0.71223 (6)	0.77354 (16)	0.76435 (7)	0.01927 (19)
C1	0.65506 (8)	0.5945 (2)	0.70453 (10)	0.0274 (2)
H1A	0.616934	0.656109	0.635647	0.041*
H1B	0.620479	0.536110	0.751545	0.041*
H1C	0.689597	0.471912	0.686470	0.041*
C2	0.77022 (7)	0.68697 (19)	0.86859 (9)	0.0219 (2)
H2A	0.811282	0.578162	0.851550	0.026*
H2B	0.736418	0.607142	0.911910	0.026*
C3	0.81920 (7)	0.8817 (2)	0.93665 (8)	0.0219 (2)
H3A	0.779377	0.970548	0.967625	0.026*
H3B	0.864966	0.820396	0.999865	0.026*
C4	0.85940 (6)	1.03588 (18)	0.86857 (8)	0.0176 (2)
C5	0.82967 (6)	1.03240 (18)	0.75240 (8)	0.0173 (2)
C6	0.76234 (7)	0.86499 (19)	0.69280 (8)	0.0201 (2)
H6A	0.7237 (9)	0.935 (2)	0.6266 (12)	0.025 (3)*
H6B	0.7924 (9)	0.735 (3)	0.6644 (12)	0.031 (4)*
C7	0.92500 (7)	1.18598 (19)	0.91984 (8)	0.0198 (2)
H7	0.945826	1.188163	0.998746	0.024*
C8	0.96030 (7)	1.33188 (19)	0.85767 (9)	0.0213 (2)
H8	1.005049	1.432594	0.893817	0.026*
C9	0.92978 (7)	1.33005 (19)	0.74177 (9)	0.0220 (2)
H9	0.953393	1.429876	0.698493	0.026*
C10	0.86485 (7)	1.18171 (19)	0.69038 (8)	0.0204 (2)
H10	0.843808	1.181363	0.611478	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0237 (4)	0.0211 (4)	0.0236 (4)	0.0030 (3)	0.0079 (3)	−0.0008 (3)
O3	0.0303 (4)	0.0251 (4)	0.0223 (4)	−0.0020 (3)	0.0086 (3)	−0.0023 (3)
O2	0.0270 (4)	0.0234 (4)	0.0255 (4)	−0.0006 (3)	0.0091 (3)	0.0030 (3)
N1	0.0197 (4)	0.0194 (4)	0.0192 (4)	−0.0010 (3)	0.0063 (3)	−0.0001 (3)
C1	0.0287 (6)	0.0240 (6)	0.0301 (6)	−0.0063 (5)	0.0092 (5)	−0.0064 (4)
C2	0.0236 (5)	0.0219 (5)	0.0219 (5)	0.0026 (4)	0.0091 (4)	0.0053 (4)
C3	0.0212 (5)	0.0287 (6)	0.0163 (4)	0.0002 (4)	0.0063 (4)	0.0056 (4)
C4	0.0176 (5)	0.0208 (5)	0.0158 (4)	0.0038 (4)	0.0068 (4)	0.0026 (4)
C5	0.0172 (5)	0.0199 (5)	0.0160 (4)	0.0038 (4)	0.0066 (4)	0.0015 (4)
C6	0.0216 (5)	0.0237 (5)	0.0157 (4)	−0.0008 (4)	0.0065 (4)	−0.0004 (4)
C7	0.0197 (5)	0.0243 (5)	0.0160 (4)	0.0034 (4)	0.0059 (4)	0.0001 (4)
C8	0.0199 (5)	0.0221 (5)	0.0230 (5)	−0.0010 (4)	0.0077 (4)	−0.0024 (4)
C9	0.0247 (5)	0.0230 (5)	0.0217 (5)	0.0008 (4)	0.0122 (4)	0.0031 (4)
C10	0.0231 (5)	0.0241 (5)	0.0157 (4)	0.0023 (4)	0.0084 (4)	0.0021 (4)

Geometric parameters (Å, º)

O1—H1D	0.94 (2)	C3—H3B	0.9900
O1—H1E	0.95 (2)	C3—C4	1.5124 (14)
O3—H3C	0.86 (2)	C4—C5	1.3977 (13)
O3—H3D	0.91 (2)	C4—C7	1.3964 (15)
O2—H2C	0.92 (2)	C5—C6	1.5081 (15)
O2—H2D	0.88 (2)	C5—C10	1.3968 (14)
N1—C1	1.4678 (14)	C6—H6A	0.980 (14)
N1—C2	1.4708 (14)	C6—H6B	1.022 (15)
N1—C6	1.4671 (13)	C7—H7	0.9500
C1—H1A	0.9800	C7—C8	1.3865 (15)
C1—H1B	0.9800	C8—H8	0.9500
C1—H1C	0.9800	C8—C9	1.3952 (15)
C2—H2A	0.9900	C9—H9	0.9500
C2—H2B	0.9900	C9—C10	1.3833 (16)
C2—C3	1.5190 (16)	C10—H10	0.9500
C3—H3A	0.9900
H1D—O1—H1E	106.2 (17)	C4—C3—H3B	109.1
H3C—O3—H3D	105.7 (18)	C5—C4—C3	119.87 (10)
H2C—O2—H2D	106.2 (18)	C7—C4—C3	121.11 (9)
C1—N1—C2	110.91 (9)	C7—C4—C5	119.01 (9)
C6—N1—C1	109.43 (8)	C4—C5—C6	121.09 (9)
C6—N1—C2	110.12 (8)	C10—C5—C4	119.45 (10)
N1—C1—H1A	109.5	C10—C5—C6	119.44 (9)
N1—C1—H1B	109.5	N1—C6—H6A	109.8 (8)
N1—C1—H1C	109.5	N1—C6—H6B	109.3 (8)
H1A—C1—H1B	109.5	C5—C6—H6A	110.2 (8)
H1A—C1—H1C	109.5	C5—C6—H6B	108.5 (8)
H1B—C1—H1C	109.5	H6A—C6—H6B	106.1 (11)
N1—C2—H2A	109.7	C4—C7—H7	119.4
N1—C2—H2B	109.7	C8—C7—C4	121.21 (9)
N1—C2—C3	109.72 (9)	C8—C7—H7	119.4
H2A—C2—H2B	108.2	C7—C8—H8	120.2
C3—C2—H2A	109.7	C7—C8—C9	119.67 (10)
C3—C2—H2B	109.7	C9—C8—H8	120.2
C2—C3—H3A	109.1	C8—C9—H9	120.3
C2—C3—H3B	109.1	C10—C9—C8	119.46 (10)
H3A—C3—H3B	107.8	C10—C9—H9	120.3
N1—C6—C5	112.77 (8)	C5—C10—H10	119.4
C4—C3—C2	112.45 (9)	C9—C10—C5	121.19 (10)
C4—C3—H3A	109.1	C9—C10—H10	119.4
N1—C2—C3—C4	−49.12 (12)	C4—C5—C10—C9	1.27 (16)
C1—N1—C2—C3	−171.72 (9)	C4—C7—C8—C9	0.23 (16)
C1—N1—C6—C5	−173.75 (9)	C5—C4—C7—C8	0.56 (16)
C2—N1—C6—C5	−51.59 (12)	C6—N1—C2—C3	67.00 (11)
C2—C3—C4—C5	18.69 (14)	C6—C5—C10—C9	−176.74 (10)
C2—C3—C4—C7	−162.56 (10)	C7—C4—C5—C6	176.68 (9)
C3—C4—C5—C6	−4.55 (15)	C7—C4—C5—C10	−1.29 (15)
C3—C4—C5—C10	177.48 (10)	C7—C8—C9—C10	−0.28 (16)
C3—C4—C7—C8	−178.19 (10)	C8—C9—C10—C5	−0.47 (16)
C4—C5—C6—N1	20.70 (14)	C10—C5—C6—N1	−161.33 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···N1	0.94 (2)	1.81 (2)	2.7394 (12)	170.7 (18)
O1—H1E···O2^i	0.95 (2)	1.81 (2)	2.7635 (12)	176 (2)
O3—H3C···O2	0.86 (2)	1.96 (2)	2.8070 (13)	165.8 (19)
O3—H3D···O1^ii	0.91 (2)	1.84 (2)	2.7461 (12)	175.1 (19)
O2—H2C···O1	0.92 (2)	1.84 (2)	2.7538 (12)	174.9 (19)
O2—H2D···O3^iii	0.88 (2)	1.88 (2)	2.7512 (13)	173 (2)
C6—H6A···O3^i	0.98 (2)	2.49 (2)	3.4531 (3)	168.8 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2.

Selected geometric parameter (Å,°)

N1–C1	1.4678 (14)	N1–C6	1.4671 (13)
N1–C2	1.4708 (14)	C4–C5	1.3977 (13)
C1–N1–C2	110.91 (9)	N1–C2–C3	109.72 (9)
C1–N1–C6	109.43 (8)	N1–C6–C5	112.77 (8)
C6–N1–C2	110.12 (8)	C4–C3–C2	112.45 (9)